Osprey FL Real Estate & Homes for Sale

Homes For Sale In Osprey FL

Opulent Exclusivity Awaits You at The Oaks, Osprey Florida. Nestled in the prestigious waterfront community of The Oaks - Bayside, 75 Osprey Point Dr. stands as a testament to luxurious living and architectural magnificence. This expansive estate....

OSPREY Homes |

MLS #A4611113

$1,795,000 | Active Home listing
4 Beds | 4 Baths | 4,001 Sqft | 1 Acres Lot

75 OSPREY POINT DRIVE, OSPREY, FL 34229 Sarasota County

When you're ready to settle down and take it easy, take a good look at Happy Haven, an age-restricted (55+), professionally managed, manufactured home community. Right now, qualifying applicants could own a 2017 model year, 800 sq. ft. 3 bed/2....

Osprey Homes |

MLS #11162680

$54,000 | Active Home listing
3 Beds | 2 Baths | 0 Sqft | 0 Acres Lot

124 Happy Haven Drive, Osprey, FL 34229

Osprey Homes |

MLS #11207261

$45,000 | Active Home listing
2 Beds | 2 Baths | 0 Sqft | 0 Acres Lot

124 Happy Haven Drive, Osprey, FL 34229

OSPREY Homes |

MLS #A4611383

$685,000 | Active Home listing
3 Beds | 2 Baths | 2,102 Sqft | 0 Acres Lot

817 PLACID LAKE DRIVE, OSPREY, FL 34229 Sarasota County

Welcome to your dream home in The Oaks Clubside. Incredible curb appeal will be your first impression of this 4 bedroom (plus office) home with 3 full and one half baths. With a pavered walkway, circular driveway, and lovely landscaping you are....

OSPREY Homes |

MLS #A4610759

$1,900,000 | Active Home listing
4 Beds | 4 Baths | 4,368 Sqft | 1 Acres Lot

451 MAC EWEN DR, OSPREY, FL 34229 Sarasota County

Welcome home to this beautiful ground floor, 2-bedroom, 2-bathroom condo, located in the gated community of Bay Street Village! With over 1,400 square feet of living space, an additional den, a separate laundry room, and a one-car garage, space....

OSPREY Homes |

MLS #A4610996

$489,000 | Active Home listing
2 Beds | 2 Baths | 1,449 Sqft | 0 Acres Lot

89 NAVIGATION CIRCLE, OSPREY, FL 34229 Sarasota County

This beautiful 3-bedroom, 2-bath house is located in The Oaks community. The house features a 2-car garage and tile flooring throughout.
The 3rd bedroom is currently used as an office with a built-in desk. Enjoy the heated pool and the....

OSPREY Homes |

MLS #A4611066

$865,000 | Active Home listing
3 Beds | 2 Baths | 2,358 Sqft | 0 Acres Lot

149 TURQUOISE LANE, OSPREY, FL 34229 Sarasota County

WELCOME TO EDGEWATER AT HIDDEN BAY! PENTHOUSE PARADISE: STUNNING WATER VIEWS OF THE INTRACOASTAL Discover unparalleled luxury and breathtaking views in this BOCA MODEL with spacious 2-BEDROOM, FLEX ROOM, & 2.5 BATHROOM home overlooking Little....

OSPREY Homes |

MLS #A4611237

$925,000 | Active Home listing
2 Beds | 3 Baths | 1,950 Sqft | 0 Acres Lot

260 HIDDEN BAY DRIVE, OSPREY, FL 34229 Sarasota County

Welcome to your slice of paradise in sunny Florida! Nestled in the heart of Sarasota County, Bay Street Village community, a highly desirable gated pet-friendly community offering maintenance-free living. This meticulously maintained 3-bed, 2-bath....

OSPREY Homes |

MLS #A4609868

$404,900 | Active Home listing
3 Beds | 2 Baths | 1,430 Sqft | 0 Acres Lot

76 EXPLORER DRIVE, OSPREY, FL 34229 Sarasota County

One or more photo(s) has been virtually staged. This is the one you've been waiting for! Nestled on 3.02 acres, this cherished family estate, spanning generations, awaits its next chapter. Situated opposite the esteemed Pine View School for the....

OSPREY Homes |

MLS #A4610560

$962,500 | Active Home listing
3 Beds | 3 Baths | 2,176 Sqft | 3 Acres Lot

510 OLD VENICE ROAD, OSPREY, FL 34229 Sarasota County

This 4 bedroom with 5 full, and 1 half bath, a new roof and fresh exterior paint, is waiting for you to come and make it your own. Situated on a beautiful lot in The Oaks Clubside, it offers stunning views overlooking the lake out to the #7 of....

OSPREY Homes |

MLS #A4610414

$1,549,000 | Active Home listing
4 Beds | 6 Baths | 4,406 Sqft | 1 Acres Lot

639 EAGLE WATCH LANE, OSPREY, FL 34229 Sarasota County

Bay Street Village is a luxurious gated community comprising over 200 condo units spread across 33 architecturally stunning apartment buildings with tile roofs and paver driveways. Nestled near the Spanish Pointe Marina, this maintenance-free....

OSPREY Townhome |

MLS #A4611077

$415,000 | Active Home listing
3 Beds | 2 Baths | 1,430 Sqft | 0 Acres Lot

116 NAVIGATION CIRCLE, OSPREY, FL 34229 Sarasota County

Beautiful 4BR/3BA/3 Car Garage Pool Home located in The Woodlands of Rivendell. This gorgeous all on one floor home is surrounded by lush natural beauty with expansive views of a large sparkling lake and a beautiful extensive preserve. As you....

OSPREY Homes |

MLS #A4609658

$1,100,000 | Active Home listing
4 Beds | 3 Baths | 2,888 Sqft | 0 Acres Lot

1193 LOST CREEK COURT, OSPREY, FL 34229 Sarasota County

**TURN-KEY, MOVE IN READY 5TH FLOOR CONDO WITH WATERFRONT AND PRESERVE VIEWS RIVALING HIGHER FLOORS** - JUST BRING YOUR SUITCASE AND ENJOY PARADISE!

Over 2200sf in the Luxury, High-Rise, Meridian Condo Complex which features 3 BEDROOMS + 3....

OSPREY Homes |

MLS #A4610203

$875,000 | Active Home listing
3 Beds | 3 Baths | 2,203 Sqft | 0 Acres Lot

385 N POINT ROAD, OSPREY, FL 34229 Sarasota County

LOCATION! LOCATION! LOCATION!.... CUSTOM DESIGNED AND BUILD by ROBERT GUENGERICH….. IMPRESSIVE HIGH CEILINGS...... CUSTOM KITCHEN WITH GRANITE COUNTERTOPS..... ELEGANT HAND-SCRAPED WOOD FLOORS...... IMPACT WINDOWS and DOORS......
Step into a....

OSPREY Homes |

MLS #A4610275

$1,299,000 | Active Home listing
4 Beds | 4 Baths | 3,160 Sqft | 0 Acres Lot

135 N CREEK LANE, OSPREY, FL 34229 Sarasota County

Situated at the end of a cul-de-sac behind the gates of The Oaks, this 4 bedroom home w/1 bedroom guest house has 2 offices, four full and two half baths, exudes warmth and charm. Beautifully set on a 26,000 ft2 verdant lot, the rich vegetation....

OSPREY Homes |

MLS #A4609703

$3,100,000 | Active Home listing
5 Beds | 6 Baths | 4,937 Sqft | 1 Acres Lot

388 BUNKER HILL, OSPREY, FL 34229 Sarasota County

Offered Turnkey furnished and equipped with everything you need to move right in. This includes a kayak, beach chairs, coolers and two bicycles. This tastefully decorated 2nd floor unit with 9-ft high ceilings has been updated throughout and also....

OSPREY Homes |

MLS #A4610314

$304,900 | Active Home listing
2 Beds | 2 Baths | 1,325 Sqft | 0 Acres Lot

207 WOODLAND DRIVE, OSPREY, FL 34229 Sarasota County

Welcome to 319 Patterson Avenue, located in the charming village of Osprey. This two-bedroom, one-bath block home is situated on a quiet road and nestled in a lush, professionally landscaped garden. This peaceful house has all you need: a great....

OSPREY Homes |

MLS #A4609331

$319,900 | Active Home listing
2 Beds | 1 Baths | 987 Sqft | 0 Acres Lot

319 PATTERSON AVENUE, OSPREY, FL 34229 Sarasota County

Welcome home to The Oaks Bayside!! This home offers the perfect blend of luxury and comfort. Fall in love with this stately two-story custom pool home. On entry, you are immediately greeted by soaring 24’ ceilings, floor to ceiling Palladian....

OSPREY Homes |

MLS #A4608902

$2,100,000 | Active Home listing
5 Beds | 6 Baths | 4,885 Sqft | 1 Acres Lot

97 SUGAR MILL DRIVE, OSPREY, FL 34229 Sarasota County

Spectacular views in all directions at highly desired Blackburn Harbor in Osprey. Tucked back and surrounded by mature and well groomed grounds you’ll park in your private under building parking space near your own large secured storage unit.....

OSPREY Homes |

MLS #N6132519

$400,000 | Active Home listing
2 Beds | 2 Baths | 1,255 Sqft | 0 Acres Lot

7102 JESSIE HARBOR DRIVE, OSPREY, FL 34229 Sarasota County

Begin each day in awe with breathtaking panoramic water views from the kitchen, living room, and master bedroom suite of your stunning fifth-floor condo in Blackburn Harbor!

Take leisurely strolls through the lush landscaped walkways of this....

OSPREY Homes |

MLS #A4609536

$639,000 | Active Home listing
3 Beds | 2 Baths | 2,143 Sqft | 0 Acres Lot

5100 JESSIE HARBOR DRIVE, OSPREY, FL 34229 Sarasota County

*IMMACULATE, MOVE-IN READY, FURNISHED , POOL AND PALM TREES VIEW**
Welcome to life in paradise! Here's your best opportunity yet! TURN-KEY FURNISHED

OSPREY Townhome |

MLS #A4608521

$399,999 | Active Home listing
3 Beds | 2 Baths | 1,430 Sqft | 0 Acres Lot

4212 EXPEDITION WAY, OSPREY, FL 34229 Sarasota County

Discover an exclusive enclave of 2-bedroom, 2 full bath villas, with no age or pet restrictions, nestled within the picturesque Sorrento Shores community. With 28 units in total, residents enjoy access to the community dock with 6 Boat Slips and....

OSPREY Homes |

MLS #A4605847

$585,000 | Active Home listing
2 Beds | 2 Baths | 1,411 Sqft | 0 Acres Lot

117 VILLA DRIVE, OSPREY, FL 34229 Sarasota County

Welcome to Hidden Bay. This stunning 3bd/ 3br corner unit condo offers unimpeded views of Casey Key and Little Sarasota Bay from many rooms. The large foyer welcomes guests into the home and boasts a completely remodeled 5th floor unit featuring....

OSPREY Homes |

MLS #A4606868

$975,000 | Active Home listing
3 Beds | 3 Baths | 2,100 Sqft | 0 Acres Lot

236 HIDDEN BAY DRIVE, OSPREY, FL 34229 Sarasota County

One or more photo(s) has been virtually staged. Under Construction. Photos are for demonstration purposes only and may not reflect the actual unit or floor plan in the building. Located on the water's edge of Little Sarasota Bay in Osprey,....

OSPREY Homes |

MLS #A4606472

$740,250 | Active Home listing
3 Beds | 2 Baths | 1,937 Sqft | 0 Acres Lot

280 HIDDEN BAY DRIVE, OSPREY, FL 34229 Sarasota County

OSPREY Homes |

MLS #A4606470

$782,250 | Active Home listing
3 Beds | 3 Baths | 2,166 Sqft | 0 Acres Lot

280 HIDDEN BAY DRIVE, OSPREY, FL 34229 Sarasota County

OSPREY Homes |

MLS #A4606463

$792,750 | Active Home listing
3 Beds | 2 Baths | 1,937 Sqft | 0 Acres Lot

280 HIDDEN BAY DRIVE, OSPREY, FL 34229 Sarasota County

TURNKEY FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside,....

OSPREY Homes |

MLS #A4605652

$275,000 | Active Home listing
2 Beds | 2 Baths | 1,325 Sqft | 0 Acres Lot

110 WOODLAND PLACE, OSPREY, FL 34229 Sarasota County

Welcome to your dream home nestled in the serene community of Bay Oaks in Osprey, Florida. This charming residence offers the perfect blend of comfort and convenience. As you approach the cul-de-sac street, you'll be greeted by the inviting curb....

OSPREY Homes |

MLS #A4605531

$600,000 | Active Home listing
3 Beds | 2 Baths | 1,977 Sqft | 0 Acres Lot

515 OAK BAY DRIVE, OSPREY, FL 34229 Sarasota County

NATURE LOVERS, welcome to the enchanting world of Pine Run! Designed to be part of the natural environment, these West of Trail condos are nestled among the lush foliage, towering trees, and Florida wildlife. Offering a peaceful and serene....

OSPREY Homes |

MLS #A4606661

$292,000 | Active Home listing
2 Beds | 2 Baths | 1,223 Sqft | 0 Acres Lot

109 WOODLAND PLACE, OSPREY, FL 34229 Sarasota County

Rarely available 1 bedroom with loft nestled in the heart of Pine Run! This unique end unit floor plan features no neighbors above or below and no shared walls for optimal privacy. The moment you step in to this warm and charming condominium home,....

OSPREY Homes |

MLS #A4605421

$209,900 | Active Home listing
1 Beds | 1 Baths | 736 Sqft | 0 Acres Lot

767 PINE RUN DRIVE, OSPREY, FL 34229 Sarasota County

Priced below bank appraisal of $1,000,000!
Located in the premier neighborhood of Southbay Yacht and Racquet, this home has been thoughtfully updated leaving you with minimal maintenance so you can truly enjoy all that fun there is to have with....

OSPREY Homes |

MLS #A4605059

$945,000 | Active Home listing
3 Beds | 2 Baths | 2,015 Sqft | 0 Acres Lot

1251 WINDWARD DRIVE, OSPREY, FL 34229 Sarasota County

DROP ANCHOR and stay forever in this 3 bedroom, 3.5 bath, intracoastal waterway home tucked away just enough to feel like you have your very own private oasis. You have deeded boat access with your own assigned boat slip where you may catch....

OSPREY Homes |

MLS #T3505796

$3,200,000 | Active Home listing
3 Beds | 4 Baths | 2,473 Sqft | 0 Acres Lot

140 N CASEY KEY ROAD, OSPREY, FL 34229 Sarasota County

Take a look at this gorgeous island style home West of the Trail in Osprey! This 2 bedroom, 2 bathroom home features a two car garage, a third of an acre corner lot, and is perfect for water sport enthusiasts with a deeded easement for....

OSPREY Homes |

MLS #A4605082

$460,000 | Active Home listing
2 Beds | 2 Baths | 1,304 Sqft | 0 Acres Lot

308 KENSEY LANE, OSPREY, FL 34229 Sarasota County

This 4 bedroom, 4.5 bath home in The Oaks Bayside has been continuously updated and redecorated over the past several years, making it a pristine, elegant showcase. This is the perfect home for the refined country club lifestyle you seek to live.....

OSPREY Homes |

MLS #A4603094

$1,995,000 | Active Home listing
4 Beds | 5 Baths | 3,912 Sqft | 0 Acres Lot

165 SUGAR MILL DRIVE, OSPREY, FL 34229 Sarasota County

**EXQUISITELY DESIGNED ESTATE BOASTS MODERN & CONTEMPORARY ELEGANCE** This FULLY UPDATED Residence features a MAIN HOUSE with 3Beds/4.5Baths plus GUEST HOUSE (1Bed/1Bath, Kitchen/Laundry, Living area) and is situated on an Oversized, Private and....

OSPREY Homes |

MLS #A4600730

$3,995,000 | Active Home listing
4 Beds | 6 Baths | 5,453 Sqft | 1 Acres Lot

601 FERNWALK LANE, OSPREY, FL 34229 Sarasota County

One or more photo(s) has been virtually staged. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and....

OSPREY Homes |

MLS #A4603773

$599,000 | Active Home listing
3 Beds | 3 Baths | 2,594 Sqft | 2 Acres Lot

401 N POINT ROAD, OSPREY, FL 34229 Sarasota County

This third-floor Hidden Bay home starts with stunning world-class views of the pool, lagoon, and swaying palm trees. Hidden Bay is a gated community and a hidden gem located just south of Sarasota on Sarasota Bay. The pool and pickleball courts....

OSPREY Homes |

MLS #A4603733

$549,000 | Active Home listing
3 Beds | 2 Baths | 1,515 Sqft | 2 Acres Lot

223 HIDDEN BAY DRIVE, OSPREY, FL 34229 Sarasota County

**BEAUTIFULLY UPDATED ESTATE with WATER VIEW and STUNNING ARCHITECTURAL DETAILS** is located in the COVETED, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Enjoy the Private and Tranquil, Lake-front setting of this Meticulously....

FL LakeFront House |

MLS #A4601618

$1,689,900 | Active Home listing
3 Beds | 5 Baths | 3,905 Sqft | 0 Acres Lot

325 OSPREY POINT DRIVE, OSPREY, FL 34229 Sarasota County

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